Methanol → HCID 86630692, compound

HRID 1915598Notes

Reaction equation

HRID 1915598 reaction equation
[Br:1][C:2]1[N:18]=[C:5]2[N:6]=[C:7]([Cl:17])[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9](Br)[N:4]2[N:3]=1.CO.C1COCC1>C(O)(=O)C>[Br:1][C:2]1[N:18]=[C:5]2[N:6]=[C:7]([Cl:17])[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 86630693HCID 86630693, compound

Product 1

HCID 86630692HCID 86630692, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 29.4 g 2,7-dibromo-5-chloro-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine, 125 ml methanol, 500 ml THF, 12.9 ml glacial acetic acid and 14.7 g of Zn/Cu pair are stirred at 45° C. After 3 and 5 hours additional portions of 7.3 g Zn/Cu pair are added. The mixture is filtered through celite and the filtrate is diluted with water and ethyl acetate. The phases are separated and the water layer is extracted with ethyl acetate. The combined organic layers are washed with saturated Na2CO3 solution, dried over Na2SO4 and the solvent is evaporated. The solid residue is stirred in a mixture of 2-propanol/ethanol (3:1) for 2 h. The crude product is filtered and dried and is used without further purification.

Workup

  1. filtrationThe mixture is filtered through celite
  2. additionthe filtrate is diluted with water and ethyl acetate
  3. customThe phases are separated
  4. extractionthe water layer is extracted with ethyl acetate
  5. washThe combined organic layers are washed with saturated Na2CO3 solution
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated
  8. stirringThe solid residue is stirred in a mixture of 2-propanol/ethanol (3:1) for 2 h
  9. filtrationThe crude product is filtered
  10. customdried
  11. customis used without further purification

Sources & evidence

ORD record
ord-cb032be2c1fb4fdaac0dac14253660d1
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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